cis-1-(3,5-bis-trifluoromethylbenzoyl)-2,3-diphenylaziridine

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 二苯乙烯类
• 英文名称: cis-1-(3,5-bis-trifluoromethylbenzoyl)-2,3-diphenylaziridine
• 英文别名: [3,5-bis(trifluoromethyl)phenyl]-[(2S,3R)-2,3-diphenylaziridin-1-yl]methanone
• 化学式: C₂₃H₁₅F₆NO
• 分子量: 435.369
• InChiKey: WKZWKEHCIGZLMK-NWIIZVJYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6
• 重原子数：
  31
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  20.1
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis-1-(3,5-bis-trifluoromethylbenzoyl)-2,3-diphenylaziridine 在 (S)-VAPOL phosphoric acid derivative 叠氮基三甲基硅烷 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 48.0h， 生成 anti-1-azido-2-[N-(3,5-bis-trifluoromethylbenzoyl)amino]-1,2-diphenylethane 、 N-[(1R,2R)-2-azido-1,2-diphenylethyl]-3,5-bis(trifluoromethyl)benzamide
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines

  摘要：

  The enantioselective ring-opening of meso-aziridines with azide nucleophiles; proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.

  DOI：

  10.1021/ja0751779
• 作为产物：
  描述：

  3,5-双三氟甲基苯甲酰氯 、 cis-2,3-diphenylaziridine 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 cis-1-(3,5-bis-trifluoromethylbenzoyl)-2,3-diphenylaziridine
  参考文献：
  名称：

  Brønsted Acid-Catalyzed Desymmetrization of meso-Aziridines

  摘要：

  The enantioselective ring-opening of meso-aziridines with azide nucleophiles; proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.

  DOI：

  10.1021/ja0751779

文献信息

• Enantioselective ring-opening of aziridines
  申请人：Antilla Jon C.

  公开号：US20090030212A1

  公开（公告）日：2009-01-29

  A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst

  一种制备环氧丙烷和亲核试剂的亲核加成产物的方法，该方法包括在双芳基磷酸催化剂存在下处理环氧丙烷和亲核试剂。
• US7799934B2
  申请人：——

  公开号：US7799934B2

  公开（公告）日：2010-09-21
• [EN] ENANTIOSELECTIVE RING-OPENING OF AZIRIDINES<br/>[FR] OUVERTURE DE CYCLE ÉNANTIOSÉLECTIVE D'AZIRIDINES
  申请人：UNIV SOUTH FLORIDA

  公开号：WO2009005775A2

  公开（公告）日：2009-01-08

  A process for the preparation of a nucleophilic addition product of an aziridine and a nucleophile, the process comprising treating the arizidine with the nucleophile in the presence of a biaryl phosphoric acid catalyst.
• Brønsted Acid-Catalyzed Desymmetrization of <i>meso</i>-Aziridines
  作者：Emily B. Rowland、Gerald B. Rowland、Edwin Rivera-Otero、Jon C. Antilla

  DOI：10.1021/ja0751779

  日期：2007.10.1

  The enantioselective ring-opening of meso-aziridines with azide nucleophiles; proceeded in the presence of a catalytic amount of a chiral phosphoric acid catalyst. The reaction affords the formation of the products in excellent yield and enantioselectivity. Preliminary mechanistic studies indicate that the active catalytic species is a chiral silane that is generated in situ.